Aminolysis of linoleic and salicylic acid derivatives with Candida antarctica lipase B: A solvent-free process to obtain amphiphilic amides for cosmetic application

Publication date: Available online 6 February 2016 Source:Journal of Molecular Catalysis B: Enzymatic Author(s): Ana Maria Mouad, Delphine Taupin, Laurent Lehr, Florent Yvergnaux, André Luiz Meleiro Porto In this biotechnological process, the fatty amides (9Z,12Z)-N-dodecyloctadeca-9,12-dienamide (3) and N-dodecyl-2-hydroxybenzamide (5), respectively derived from linoleic acid and salicylic acid were synthesized through aminolysis reactions catalyzed by Candida antarctica lipase B. These amphiphilic compounds receive great attention from cosmetic industry due to a range of beneficial properties for skin. The aminolysis reactions were performed with the esters ethyl linoleate (1) and ethyl salicylate (4) as acyl group donors and the fatty compound N-dodecylamine (2) as the nucleophilic substrate. The aminolysis reactions were carried out in a solvent-free process, which is beneficial from an environmental and economical perspective, at 65°C and reduced pressure (50mbar). Parameters as enzyme amount and substrates molar ratios were investigated and the products were monitored by HPLC analysis. The conversion rates were measured through disappearance of ethyl linoleate and ethyl salicylate. The best conversion rates (up to 95%) were obtained by adding an enzyme amount of 5.0g/mol of acyl donor group substrate and an equimolar substrates ratio (1:1). The products characterization was performed by High Resolution Mass Spectrometry, Infrared spectroscopy and Nuclear...
Source: Journal of Molecular Catalysis B: Enzymatic - Category: Biochemistry Source Type: research